Winona Holiday Rentals

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Our top choices for Winona holiday rentals

9.8 out of 10, Exceptional, (19)
"Great place to relax enjoyed feeding the dogs and ducks Accommodations were great awesome getaway "
United States
Ray T.
The price is NZ$272
includes taxes & fees
28 Dec - 29 Dec
Relaxing Country Stay with Events Welcome!

Cottage in Whitehouse

The Cottage at Dogwood Ridge.
10.0 out of 10, Exceptional, (110)
"Absolutely loved this place! So peaceful and serene. "
United States
Amy
The price is NZ$289
includes taxes & fees
28 Dec - 29 Dec
The Cottage at Dogwood Ridge.

Cottage in Tyler

Cana Cottage | Farm Stay
10.0 out of 10, Exceptional, (44)
"Good design, well maintained "
United States
William
The price is NZ$214
includes taxes & fees
15 Jan - 16 Jan 2026
Cana Cottage | Farm Stay
9.6 out of 10, Exceptional, (5)
"Wonderful little property. Everything you need and very clean and comfortable. Host was easy to work with. I would definately stay here again."
United States
Teri T.
The price is NZ$252
includes taxes & fees
9 Jan - 10 Jan 2026
Cozy Home Near Gregg County Airport & Lake Cherokee

Cabin in Tyler

Cora's Cabins
3.0 star property
9.4 out of 10, Exceptional, (157)
"Enjoyed the stay "
United States
Benito
The price is NZ$249
includes taxes & fees
28 Dec - 29 Dec
Cora's Cabins
9.0 out of 10, Wonderful, (9)
"Thelma did a great job of taking care of us. The hot tub was amazing. A good place to get away from the everything. Pet friendly. "
United States
Benny G.
The price is NZ$228
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy cabin in charming Hawkins with AC
9.8 out of 10, Exceptional, (37)
"Very cute little cabin"
United States
David s.
The price is NZ$258
includes taxes & fees
30 Dec - 31 Dec
The Happy Pine Cone :)
10.0 out of 10, Exceptional, (21)
"Loved the loft- clean and secure. "
United States
Jessica H.
The price is NZ$460
includes taxes & fees
27 Jan - 28 Jan 2026
Chic Suite in Central Longview King Bed

Holiday Home in Kilgore

The Skelly Hideout
10.0 out of 10, Exceptional, (2)
"Will definitely be staying again . Quiet area ;)"
United States
Dreamy Y.
The price is NZ$372
includes taxes & fees
25 Jan - 26 Jan 2026
The Skelly Hideout
9.6 out of 10, Exceptional, (36)
"I was looking for a few days of weekday retreat and found it. There were a few other guests on the property but it still was quiet and peaceful. If you're looking for an escape from Dallas Fort Worth that's not an all day drive then this is it!"
United States
Marc A.
The price is NZ$276
includes taxes & fees
28 Dec - 29 Dec
The Lazy Squirrel Cabin
9.4 out of 10, Exceptional, (23)
"Very nuce perfect size for just the husband and I. Could have used just a little more privacy in the front sitting area oitside. But overall, great experience. "
United States
Jennifer W.
The price is NZ$245
includes taxes & fees
28 Dec - 29 Dec
Cozy Tiny Home in Heart of Big Sandy
10.0 out of 10, Exceptional, (3)
"Very cute place with everything we needed for a peaceful and relaxing stay. The stars and moon were beautiful that night out in the country. "
United States
Jennifer G.
The price is NZ$234
includes taxes & fees
24 Jan - 25 Jan 2026
Home away from Home- Near Tyler Airport

Holiday Home in Longview

Treehouse at Berry-patch
8.4 out of 10, Very good, (6)
"Bed was super comfy, shower was amazing, and the only thing that was missing was nice weather so we could sit on the porch in the morning. Very clean, really nicely decorated, felt like home. "
United States
Leslie K.
The price is NZ$357
includes taxes & fees
25 Jan - 26 Jan 2026
Treehouse at Berry-patch
10.0 out of 10, Exceptional, (33)
"Our family had a great time staying here! The kids LOVED the loft, the sheep, & the livestock guardian dog Roxy! "
United States
Kayla B.
The price is NZ$227
includes taxes & fees
7 Jan - 8 Jan 2026
Guesthouse on peaceful 11+ acre homestead! Pet friendly!
9.6 out of 10, Exceptional, (10)
"Very nice rental "
United States
michael S.
The price is NZ$232
includes taxes & fees
25 Jan - 26 Jan 2026
The Carriage House, The Carriage House at Jeter Farmhouse

Cabin in Tyler

The Tree House Cabin
9.6 out of 10, Exceptional, (25)
"Very nice and quiet place to stay. Was as described in listing. Would stay again."
United States
Jim M.
The price is NZ$285
includes taxes & fees
4 Jan - 5 Jan 2026
The Tree House Cabin
9.0 out of 10, Wonderful, (6)
"Great location, very nicely appointed…definitely recommend…"
United States
Harold
The price is NZ$270
includes taxes & fees
28 Dec - 29 Dec
Historic House, modern amenities and large front porch, short walk downtown

Cottage in TYLER

The Floret Cottage
10.0 out of 10, Exceptional, (2)
"Great location! We enjoyed the wonderful amenities and personal care services offered! "
United States
Kimberly G.
The price is NZ$506
includes taxes & fees
28 Dec - 29 Dec
The Floret Cottage
9.4 out of 10, Exceptional, (3)
"Clean home, excellent host"
United States
Ashley S.
The price is NZ$374
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house on quiet street in delightful Kilgore
9.2 out of 10, Wonderful, (30)
"Beautiful location tiny home is immaculate condition. It was only an overnight trip, but it was well worth it. Will be looking forward to another stay when possible."
United States
Jeffry A.
The price is NZ$300
includes taxes & fees
30 Dec - 31 Dec
Cozy tiny home in the pines - 20 minutes from Canton and Lake Fork!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winona Hotel Reviews

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as NZ$198 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Mrs. Lee's Daffodil Garden, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winona has to offer?

Cozy 2 bedroom 2 bath duplex near UT Tyler!: This holiday home rental outside of Winona is located on a lake, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Winona?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Winona stay.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Santa Land, or get out into nature at a spot like Mrs. Lee's Daffodil Garden. Tyler State Park and Jarvis Christian College are a couple of places you'll find in the wider area.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.